Henry married the 15 year old Margaret Beaufort (1443-1509) on 3 January 1458 at Maxstoke Castle, Margaret was the daughter of John Beaufort, 1st Duke of Somerset (killed at St Albans in 1455), widow of Edmund Tudor (killed at Mortimer’s Cross in 1460) and mother to the infant Henry Tudor, later Henry VII. Household accounts and personal letters indicate that the marriage was a happy one with the couple rarely apart and unusually for the period they always celebrated their wedding anniversary. They lived initially at Bourne Castle in Lincolnshire.

Henry fought at the Battle of Towton on the Lancastrian side but survived and was later pardoned by Edward IV on 25 June 1461.

Shortly afterwards, Edward IV purchased Henry Tudor’s wardship for £1000.00 and placed him in the Household of William Herbert, Earl of Pembroke, a staunch Yorkist.

In 1466, and to celebrate the marriage of Henry Stafford, 2nd Duke of Buckingham to the Queen’s sister, Edward IV presented Henry and Margaret with Woking Old Hall, a palatial house in Surrey which became their principle residence. His brother John, with whom he remained close, was a regular visitor at Woking Old Hall “to hunt and play cards”. Their staff included fifty servants, many of them “gentle born” including their Receiver-General Reginald Bray (d.1503) who went on to fight for Henry Tudor at Bosworth in 1485.

In May 1467 Henry was summoned to attend the Royal Council at Mortlake Palace and in May 1468 Henry and Margaret were again in London, staying at the Mitre Inn in Cheapside to hear the Kings public announcement of his intention to invade France, an invasion that was subsequently postponed until 1475.

In 1468 he attended Lord Scales at the Grand Tournament against the Bastard of Burgundy along with his young nephew, Henry, Duke of Buckingham.

On 20 December 1468 later Edward IV paid the couple the ultimate compliment of visiting Old Woking Hall to attend a hunt and afterwards dined with them at their hunting lodge at Brookwood. Household Accounts show that they ate in a tent of purple sarsenet serenaded by the royal minstrels. Conger eel, lamprey and 700 oysters were served off a pewter dinner service bought specially for the occasion

Although unwell, Henry is believed to have suffered from the skin disease “St Anthony’s Fire”, erysipelas (believed at the time to be a form of leprosy), he was with Edward IV on 12 March 1470 at the Battle of Losecoat Field where the rebel forces of Sir Robert, Lord Wells (Margaret Beaufort’s stepbrother) were defeated. Papers found on the battle provided clear evidence at to Warwick and Clarence’s involvement in the Lanacastrian uprising and Henry rode with the King throughout April during the pursuit of Warwick and Clarence which culminated in their flight to Calais. Shortly afterwards Henry visited Maxley to advise Margaret’s mother, Lady Wells, the news of her son’s execution.

In September 1470, Warwick and Clarence were once more on English soil. Edward, caught out by the speed of their invasion, was forced to flee into exile. Henry Stafford though initially arrested was released shortly afterwards following petition from his wife. On 27 October, Henry, Margaret, Henry Tudor and his uncle, Jasper attended the redemption of Henry VII at Westminster and dined at the palace. Margaret suddenly found herself part of the Royal Family and henceforth she would dedicate herself to the Lancastrian cause and the enhancement of her son, Henry Tudor.

On 24 March, the Duke of Somerset visited Henry and Margaret, his first cousin, at Woking Old Hall in an attempt to persuade Henry to join the Lancastrian army being mustered to defend against Edward’s inevitable return. Henry was in no mood to commit and subsequently sent retainers to Somerset’s headquarters, with instruction to discuss matters for as long as possible and delay the issue.

However on April 12 he was in London to greet Edward on his triumphant entry into the city and had by then made up his mind to join him, accompanied by the Steward of his Household, John Gilpyn, and other retainers. He was so unprepared for campaign that not only was his harness incomplete, having to send for the chain mail gussets that protected the vulnerable joints; he also had to purchase a horse for Gilypn. Mindful of his narrow escape from Towton he ordered ten of his men to wait for him at Kingston-upon-Thames to ensure, that should things go badly, he was assured of being able to cross Kingston Bridge in a hurry.

Although choosing the winning side, Henry was so badly wounded at Barnet that he never recovered and died in his bed on 14 October 1471. In his will he bequeathed thirty shillings to the Parish Church at Old Woking, a set of velvet horse trappings to his stepson, Henry Tudor, a bay courser to his brother, the Earl of Wiltshire, another horse to his receiver-general, Reginald Bray and £160 for a chantry priest to sing Masses for the repose of his soul. The rest of his estate went to “my beloved Margaret”.

John Gilpyn also survived Barnet and continued serving at Woking Old Hall until his death in 1500. Many other Stafford retainers, including John and Richard Harper and John Kymer, also remained loyal to Margaret. John Kymer and John Harper both were involved in the Exeter rising in support of the 1483 rebellion (see 2nd Duke of Buckingham) and both later went on to fight under Sir Reginald Bray at Bosworth in 1485.

Margaret Beaufort’, whose son was now the only surviving Lancastrian claimant to the throne, sent her son into exile in France and in 1472 she married Thomas, Lord Stanley.